THE ANION OF THE S-2,6-DIMETHYLMORPHOLINO)-(METHYL)CARBENE]CHROMIUM COMPLEX IN THE REACTIONS WITH NITROALKENES

Authors
LICANDRO E MAIORANA S CAPELLA L MANZOTTI R PAPAGNI A PRYCE M GRAIFF C TIRIPICCHIO A
Citation
E. Licandro et al., THE ANION OF THE S-2,6-DIMETHYLMORPHOLINO)-(METHYL)CARBENE]CHROMIUM COMPLEX IN THE REACTIONS WITH NITROALKENES, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (10), 1998, pp. 2127-2133
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY → ACNP
ISSN journal
1434193X
Issue
10
Year of publication
1998
Pages
2127 - 2133
Database
ISI
SICI code
1434-193X(1998):10<2127:TAOTSC>2.0.ZU;2-Z
Abstract
The diastereoselective Michael addition of the title anion to alpha-hy drogen- and alpha-methyl-substituted conjugated nitroalkenes leads to new gamma-nitrocarbene complexes and gamma-hydroximoamides, respective ly. The gamma-nitrocarbene complexes can be quantitatively oxidized to gamma-nitrobutyric acid derivatives (precursors of GABA derivatives); the gamma-hydroximoamides are formed as a result of an unexpected int ramolecular transfer of an oxygen atom from the nitro group to the car bene atom, with elimination of the pentacarbonyl-chromium(0) group, wh ich is recovered in high yield as the PyCr(CO)(5) complex.